Dimethylamine → HCID 59242057, compound

HRID 1876162Notes

Reaction equation

HRID 1876162 reaction equation
Cl[C:2]1[N:11]=[C:10]([N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:22])[CH:8]=2)[N:3]=1.[CH3:23][NH:24][CH3:25]>CC(O)C>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([N:12]([CH3:13])[C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[C:7]([CH3:22])[CH:8]=3)[N:3]=[C:2]([N:24]([CH3:25])[CH3:23])[N:11]=2)=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 113928514-Quinazolinamine, 2-chloro-N-(4-methoxyphenyl)-N,6-dimethyl-

Product 1

HCID 59242057HCID 59242057, compoundYield 26.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of (2-chloro-6-methyl-quinazolin-4-yl)-(4-methoxyphenyl)-methyl-amine (64.4 mg, 0.21 mmol) and dimethylamine (2.0 M in THF, 1.0 mL, 2.0 mmol) in i-PrOH (2 mL) was heated to 100° C. overnight. After cooling to room temperature the reaction was concentrated onto SiO2 and purified by gradient MPLC (SiO2, 0 to 10%, MeOH/CH2Cl2, 20 min). 17.9 mg (26%) of the title compound was obtained: 1H NMR (DMSO-d6) δ 7.17-7.28 (m, 2 H), 7.12-7.16 (m, 2 H), 6.95-7.01 (m, 2 H), 6.51-6.54 (m, 1 H), 3.77 (s, 3 H), 3.44 (s, 3 H), 3.19 (s, 6 H), 1.94 (s, 3 H). HRMS (ES) calcd for C19H23N4O [(M+H)] 323.1866, found 323.1951.

Workup

  1. concentrationwas concentrated onto SiO2
  2. custompurified by gradient MPLC (SiO2, 0 to 10%, MeOH/CH2Cl2, 20 min)

Sources & evidence

ORD record
ord-d4af76aca78142a5a162f2fcbf47c46e
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

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